Tetrabutylammonium Fluoride → HCID 57828216, compound

HRID 1644226Notes

Reaction equation

HRID 1644226 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C>C1COCC1>[OH:26][C:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:30]([CH2:37][CH2:38][CH2:39][CH2:40][NH:41][C:42](=[O:51])[O:43][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57828239HCID 57828239, compound

Product 1

HCID 57828216HCID 57828216, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammoniumfluoride (1.0 M in THF, 1.1 mL) was added to a solution of benzyl 4-[4-(tert-butyldimethylsilyloxy)naphthalen-1-yl]butylcarbamate (19, 500 mg, 1.1 mmole) in THF (5 ml) at room temperature. The reaction mixture was stirred for 2 h. The reaction mixture was concentrated to dryness. The residue was purified by column chromatography (silica gel, 3:1 hexanes/EtOAc) to afford carbamate 20 (230 mg, 61%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 8.25 8.21 (m, 1H), 7.91 (dd, J=6.6, 1.8 Hz, 1H), 7.52-7.43 (m, 2H), 7.35-7.27 (m, 5H), 7.05 (d, J=7.5 Hz, 1H), 6.72 (d, J=7.5 Hz, 1H), 5.10 (s, 2H), 4.75 (br s, 1H), 3.23 (q, J=6.6 Hz, 2H), 2.95 (t, J=7.2 Hz, 2H), 1.76-1.56 (m, 4H).

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe residue was purified by column chromatography (silica gel, 3:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-c925052f54de4114afa3438619a4fd26
Source dataset
uspto-grants-2012_02
Patent number
US08124607B2

Reaction notes

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